Mixed 3-Heptenes

The reaction of 3-bromo-5-(methylthio)-2-methylselenophene (61) with ethyllithium and ethyl bromide (Eq. 18) gives mixed thioselenoacetals of an acetylenic ketene (62) in high yield.80 Similarly, isomeric 3-bromo-5-methyl-2-(methylthio)selenophene (63) is also easily cleaved to give 2-ethylseleno-5-methylthio-2-hepten-4-yne (64) (Eq. 17). Such compounds are difficult to obtain by other methods. 

EINECS 246-871-2 Heptene Heptene (mixed cis and trans) Heptylene. 

American companies became interested in the process during the war and initiated a substantial research program. Since production of specific alcohols was desired, more attention was focused on the use of narrow cuts of individual olefins in contrast to the mixed feeds employed by the Germans. The first commercial plant in the United States was constructed by the Standard Oil Company at Baton Rouge, La., in 1949. The main product from this plant is isooctyl alcohol produced from a heptene feed. As shown in Table 11-9, additional plants have been constructed by other large petrochemical companies, and the combined annual capacity at the end of 1956 exceeded 100 million lb of alcohols. In addition to isooctyl alcohol, the American plants produce normal and isobutyl aldehydes and alcohols, decyl and tridecyl alcohol. ... 

The pure 3-heptene experiments were done on l.OM solutions in pentane. The pure 3-hexene experiments were done on 0.5M solutions in pentane. The mixed hexene and octene experiments were done on pentane solutions which were 0.5M in each olefin. The added aldehyde experiments were done on pentane solutions which were 0.5M in olefin and of varying concentrations of the aldehydes. The ozonides were identified as previously described 11). Ozonide yields were obtained by calibrating the GLPC peak areas with known weights of the ozonides. The elemental analysis of hexene-3 ozonide was previously reported 11). Analyses for heptene-3 and octene-4 ozonide were obtained. 

Here again, the 3-hexene ozonide cis-trans ratio depends on the origin of the ozonide. The same general observations that were found for 3-heptene ozonide also apply here. Thus, the all-cis olefin pair gives a higher percentage ci5-3-hexene ozonide than the all-trans pair, while the two mixed isomer pairs give ratios which fall between those for the all-cis and all-trans cases. 

Such a-olefins as (+)- S)-3-methyl-l-pentene, (—)(S)-4-(methyl-l-hexene, and (+ )(S)-5-methyl-heptene have been polymerized with a titanium trichlo-ride/tri-isobutylaluminum catalyst without solvents. From the product mix, by solvent extraction crystalline and amorphous fractions were isolated. Both forms... 

The measurements were performed with extrapolation to zero dilution of the sorbate (heptene, benzene). The following equation was used to calculate the mixing thermodynamic parameters ... 

Commercial olefins that are essentially mixtures of aliphatic mono-olefms and that fall within the range of 95 to 165 bromine number (see Note 1). This test method has been found suitable for such materials as commercial propylene trimer and tetramer, butene dimer, and mixed nonenes, octenes, and heptenes. This test method is not satisfactory for normal alpha-olefins. 

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